Who I’d like to meet:

Details:

It’s that time of year in nyc. Beautiful weather and amazing concerts. I made it to four great ones last week, including three days in row to end the week.

On Thursday, some friends and I went out to Williamsburg to watch Ok Go!. First time seeing them live, and my first time at the Music Hall of Williamsburg. It won’t be the last. They put on an amazing show full of lasers, church bells and great music.

On Friday, we went to fun., one of my favorite bands to watch live. Unfortunately, they weren’t the headliner so the crowd wasn’t quite as in to them as they should have been. If you’ve never listened to them or watched them live, you’re missing out. (This clip is from a show we went to last year at Mercury Lounge.)

With the holidays just around the corner, I’ve been thinking a lot about my family and friends back home. I’m spending the holidays with my girlfriend and her family this year, so I won’t be able to make it back to my hometown. It can be hard living across the country from where you grew up, especially when you grew up in a small town as I did.

But as I sit here thinking about “home,” I can’t help but realize how much of an impact my roots have on my excitement toward what we’re building at OpenSky.

I’m from California, but not likely the California you know. San Diego, Los Angeles, San Francisco, and Napa Valley get all of the glory, but if you’re willing to take a drive up north, well north of the beaten path, you’ll find a town where the old way of life has not been compromised. 300 miles up the highway from San Francisco, nestled in a small valley between two redwood forests, is my hometown.

Ferndale, California, or the “Victorian Village,” as it is known, is a thriving dairy community with a population of just 1,350. True to its namesake, Ferndale has old-fashioned mercantiles with Victorian architecture, a local market, a leather shop, and even a real-life blacksmith. There are no traffic lights, chain restaurants, or big-box retailers. I grew up on “Ambrosini Lane” and the name of the main street in town is actually “Main Street.”

As described in a brochure, “Ferndale is a working, all-American town which takes pride in its beautiful community and cultural heritage. In the late 1800s Ferndale was an agricultural and transportation center, a melting pot for Scandinavian, Portuguese and Swiss-Italian [that’s me!] immigrants.”

For those who visit, it’s an untouched remnant of a way of life that used to be; Main Street stuck in time. But my nostalgic thoughts of Ferndale aren’t about local brick-and-mortar shops or picturesque snapshots of yesteryear. Sitting here 3,000 miles away, my memories of Ferndale are about community: about someone taking the time to smile and offer a kind greeting; about meaningful and trusted relationships, old-fashioned service and friendly faces; about passionate shopkeepers who care about the people they serve.

And that is why I’m so excited about OpenSky. It is everything I love about Ferndale, but without the geographic limitations. Relationships today are not restricted to the area in which you live, and that may be the single most powerful impact the Internet has had on the world.

For years, we were excited that the Internet gave us instant access to infinite information. It was new. But the novelty wore off. It was information overload; just noise with no personal connection to you. And now we’ve come full circle. People value relationships again. Relationships drive human interaction online, just as they do offline. They are the key to both social communities (think Facebook) and commerce communities (OpenSky).

Ferndale represents relationship commerce, something that went missing as the world moved online. OpenSky is bringing relationship commerce back… online. For me, it’s home away from home.

Last week, the NY Times had an article about how Amazon is successfully becoming the Wal-Mart of the web.

It’s an interesting comparison.

Wal-Mart was founded in 1962 as a discount department store. It is now the world’s largest public corporation (by revenue), and is the United States’ largest grocery retailer and private employer.

Amazon was founded in 1994 as an online bookstore. It is now the largest online retailer in the US. Moreover, sales of media products in the US — the books, movies and music that it started with — has been surpassed by sales of other merchandise on the site. Soon the same will be true worldwide.

What began as an online bookstore has become the biggest online general store.

According to the article, many believe this is a great place for Amazon to be and has caused its rivals to scramble to compete:

In August, Target, which allowed Amazon to run its Web site for the last decade, announced it would end the affiliation when its contract was up in 2011, following other one-time Amazon partners like Borders and Toys “R” Us. This month, Wal-Mart said it would allow other retailers to sell their products on Walmart.com, mimicking Amazon’s third-party marketplace and trying to match its vast selection. Analysts believe Sears, which owns Kmart, is preparing to allow outside sellers on its sites as well.

But the Amazon effect may be most deeply felt by small independent stores, which cannot hope to compete with Amazon’s selection and prices and recall in fear how the company hastened the fate of both independent booksellers and prominent electronics chains like Circuit City.

It seems the retail giants are in a race to see who can offer the biggest online selection of goods, the first to reach “the holy grail” that is endless lists of products. It’s a race that Amazon is winning and from which it is building a big business ($40 billion big!).

However, the article goes on to highlight that in niche, passionate categories these massive lists of products do not create the same advantages for Amazon and other retail giants:

In markets like consumer electronics, where Amazon increasingly prevails, products like HDTVs from different companies are usually made by the same Asian factories, with little technical difference between brands. Shoppers then look for the best price and most convenient delivery, which Amazon can offer.

But the dynamics are different in categories like outdoor sporting goods. Different companies offer drastically different products, and the right brand of bicycle or snowboard matters to enthusiasts. Shoppers might also prefer to seek the guidance of an experienced sales clerk.

For many of us, and for many passion categories, shopping is more than a transaction. It’s an experience, an extension of our passion. It’s meaningful and thrilling. For us, Amazon and Wal-Mart leave us longing for more.

Sam Walton, the founder of Wal-Mart, once said “Each Wal-Mart store should reflect the values of its customers and support the vision they hold for their community.” I’m not sure this holds true today, making the Amazon comparison even more interesting. In response to Walton’s quote, Matt recently wrote:

Wal-Mart isn’t the same place as when Mr. Sam was alive. He understood that shopping is about people. You won’t find that feeling at Wal-Mart today, as humanity and expertise has been brushed aside in favor of large amounts of inventory and self-serve checkout lanes. Get in, get your stuff, and get out.

…Shopping needs it’s humanity back. There are still some stores that offer a human experience — John discovered a magic shop in New York City that does. We remember these experiences, where a passionate shopkeeper brightened our day, gave generously of his time and expertise, and inspired us to share in his passion. We almost always leave with a bag in our hand and a smile on our face. We pass the story on to our friends and family.

OpenSky is bringing it back, and taking it online.

OpenSky and its network of expert shopkeepers don’t aspire to be the Wal-Mart of the web.

OpenSky aspires to connect consumers to experts and the products they love. OpenSky aspires to bring humanity back to shopping.

One of my favorite aspects of living in nyc is the music scene. The venues here are amazing, the atmosphere unparalleled.

Last night I checked out fun. playing a show at Mercury Lounge. I’ve been a fan of Nate Reuss, the lead singer, for some years by way of his previous band The Format. He always puts on a good show and last night he did not disappoint.

Nate, whose voice is reminiscent of that of Freddie Mercury’s, reaches unreachable high notes followed immediately by soft ones, all the while making you feel emotions that you didn’t know existed. Every single person in the crowd was completely lost in the moment, feeling every beat and emotion. His stories are inspiring, emotionally loaded and have a passionate champion to bring them to life.

What struck me as I was leaving was how truly authentic of an experience it was. Nate and crew are entertainers being paid to perform, but it was clear that none of them were on stage for any reason other than passion. Today they tweated: @ournameisfun “Had a sickyicky time at the mercury lounge. We are very lucky dudes.”

Einstein never had the opportunity to experience ecommerce, but his wisdom lives on. Ecommerce is best described as endless lists of products. Incredibly efficient. And as algorithms have become more advanced, ecommerce has become even more efficient. In today’s fast-paced, price-conscious world efficiency is essential, without doubt, especially as it relates to everyday goods.

But the brilliance of humans has been lost among these massive online lists of products. For many of us, shopping is more than a transaction. Its an experience, an extension of our passion. Its community, interactive and trusted. Its meaningful and thrilling.

It’s why we started OpenSky. For us, human shopping is a welcome change.

I, for one, am excited about the upcoming market challenges facing start-ups.Yes, less money will be invested.Yes, valuations will be lower.And yes, start-ups will have to run leaner even if at the expense of growth.Good.

As a fan of technology and innovation, I’m bored.I’ve been bored. The past few years have been littered with over-hyped, over-funded “companies” (please note the quotations) that are much better suited as plug-ins or features than real businesses. Everyone knows this, but the tech community prides itself on building “the next big thing”.So it’s compelled to throw catchy language around in an attempt to convince itself that we are continually entering new stages of development.Web 2.0.No, Web 3.0.No, cloud computing!

But no matter how or how often you say it, the fact is innovation has stalled. Rather than building disruptive technologies that can transform an industry, entrepreneurs have focused on the race to be the latest [insert hyped trend here] company featured on Techcrunch.Why? Because Techcrunch = hype, hype = VC money, VC money = more hype, and more hype = a quick flip.It’s a beautiful equation, but one that only works with excess VC money, growing budgets, and dying incumbents that are scared shitless.

Even if you exclude the “me-too” noise, what we’ve been experiencing for the last several years is, at best, simply the natural evolution of previous innovation: adding a new feature, designing a better UI, expanding into new markets…making current technologies incrementally better or more useful.Necessary? Of course.Exciting? Not the slightest. I’m bored of incremental.

[Enter the current economic crisis]

The climate has changed.There is a cautious attitude among investors (if not an actual strain on VC money), budgets are declining and exits of any kind are years away (at least for money losing start-ups).

Now this? This has the potential to be exciting.With funding hard to come by and quick exits but a memory, the noise will fade.Only real business models with true long-term value creation potential will get funded.And only smart, passionate (yet prudent) entrepreneurs—those willing to risk it all for something they truly believe in—will survive.Long-term perspective and passionate minds is a beautiful combination, one that leads to the creation of disruptive technologies and ideas.

Almost exactly three years ago, when I was but just a small town kid from California trying out life in the big city, I posted to my blog:

…what a great setting: a beautiful, sunny Saturday afternoon in New York City with The Shore providing my real life soundtrack. I’ve literally been sitting here for the last couple of hours relaxing, listening to music with a smile on my face because I can’t get over how much I love New York City.

It’s funny: somehow when you live here you are able to forgive, let go unnoticed even, all the obnoxious horn-honking, uncomfortable 8×8 boxes we call apartments, garbage-lined sidewalks, 8mm+ suits/hipsters/tourists constantly rushing toward their destinations (with no interest in seeming friendly), unbearable humidity, and lack of direct contact to sunlight. Instead, we relax listening to music on sunny Saturday afternoons with smiles on our faces, because we know that never before or ever again will we have as much fun as we are having right now.

Well I’ve decided I’m not quite done with the city just yet. So I’m back!

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It was one and a half years ago that I left New York to join a small start-up I had invested in at my previous firm. The transition from NYC to a tiny suburb of Sacramento was tough (read as: unbearable), but being involved with MaxPreps was a privilege and an experience that I feel very fortunate to have… well… umm… experienced.

In 2005, while I was at a NYC-based venture capital firm, I developed the thesis that the Internet was not only enabling a dramatic shift in local media, but that shift was going to be largely realized in the coming one to three years. The infrastructure had been in place, but the timing of the market was beginning to feel right. Historically, traditional local media (newspapers and television) owned “the local”.They had built huge brands over the years and had a lock on distribution…but the Internet had/was changing that, especially with regard to the lock on distribution. Readers/users were simply finding their information sources elsewhere.

I wasn’t revolutionary in this belief by any means.Craigslist was already well established and there was a crop of early stage companies in the hyperlocal community space being funded: Judy’s Book, Insider Pages, Yelp, etc. Further, Google and Yahoo! had even begun working on their local strategies. In fact, many verticals once dominated by local media were being attacked by new media: classifieds, weather, traffic, business reviews, etc.

Generally, the model was to leverage the community to provide low-cost content and a centralized database to publish the data in a local manner.The geo-targeted content created a huge value proposition to local advertisers…and by aggregating the hyperlocal communities you also created an audience large enough to attract national advertisers.All of this (including the instant, on-demand information access aspect) at a cost structure that completely disrupted the traditional print and broadcast models.

However, most verticals already had a dominant leader or were crowded with well-funded start-ups.Further, it wasn’t clear to me how to pick a winner; most companies didn’t have any real tech or product differentiation and there was no clear home-run marketing strategy.

In the process of researching the different verticals, I came across high school sports.It was a large and established market: there are over 20,000 high schools across the country (each with a built-in, passionate fan base) and hs sports are not a trend, but rather a tradition, an institution.Also, it was clear that both local and national advertisers were interested because they had been spending money on local hs sports for years: it is a great way to reach a young demographic that has large spending power, especially in combination with the influence teens have over their parents’ spending.Further, it was a relatively untapped market.There were only a few players that had any real traction in the space and most players were still focused on the pro and college sports markets. Finally, there were obvious exits when you looked at traditional media because they needed properties to grow their younger audiences and/or extend their sports brands down market.

I had found my niche, vertical market.

MaxPreps, even in its infancy, had already attracted a decent sized audience and some major brand advertisers. More appealing was that MaxPreps had real technology, product and network/distribution differentiation: they provided a free web-based platform to high school coaches allowing them to quickly and easily input their information (schedules, scores, stats, rosters, etc.). An important aspect of this model was that they didn’t have to try and dramatically change coach behavior…coaches have always kept records of this information, MaxPreps just provided a more efficient way of doing it. The service also provided other value added features (such as content syndication to local media, text-to-mobile messaging to players, etc.) that appealed to coaches and gave them incentive to participate. With over 25% of every high school football coach already inputting data into their system, MaxPreps had already built a large user base of semi-professional content creators/providers.And there was a clear marketing strategy to grow the coach network by acquiring coaches geographically and across new sports (there was actually a known cost per coach acquisition and a direct correlation between an incremental coach and traffic growth). Once you built the network of coaches you owned the market.

Meeting Andy Beal, the company’s founder/CEO, and the rest of the MaxPreps employees only solidified my interest. It was a team of coaches and tech professionals that truly understood their customer, market and technology.I found this to be of great importance because I knew a) the traditional leaders in the space, local newspapers, were not going to move fast enough, and b) even if a new group of Silicon Valley developers, executives and investors ultimately saw the opportunity, they would not understand the market well enough to succeed. MaxPreps had all the right pieces.

Once we made the investment, I was able to observe the company much more closely and I just fell more in love with the team and the vision.A few months later, after talking with Andy, I was given the opportunity to be part of the team…so I decided to re-locate to Cameron Park (CA) and join the company full-time to help execute on some new initiatives.

A year and a half—and a highly successful exit to CBS—later, I had had one of the best professional experiences in my career. It was my first entry into operations and I was lucky enough to do it with an amazing group of people.I truly am thankful for the opportunity.

However, now I’m ready for my next new adventure.So I’m back in the city ready to listen to music on sunny Saturday afternoons with a smile on my face, knowing that never before or ever again will I have as much fun as I am right now.

From late November through January, I had slowly been building a position in Yahoo!, starting in the mid-20s all the way down to the high teens. And I was looking forward to continuing buying up shares as it dipped into the mid-teens. Why?

Here is what I like about the business:

1) Great consumer web services: Yahoo! is the market leader here. Between its homepage, email, news, finance, sports, maps, messenger, flickr, delicious, go/mobile, etc., Yahoo! has a lot of great properties and still draws the largest audience. Integration hasn’t been great and they haven’t monetized the properties through advertising as well as you’d hope…but they are still very valuable assets.

2) Great international assets: I didn’t think the market was properly valuing Yahoo! considering its stakes in Yahoo! Japan and Alibaba.

However, as a stand-alone business there still needs to be some major restructurings to ultimately realize the full long-term value. First, cut the fat (much more than the hundreds laid-off in early January) by eliminating non-revenue generating businesses (opposed to broad, blind layoffs across the entire company). Second, re-create an engineer/developer culture. Third, once the non-revenue generating products are cut, focus on integration across core products with an emphasis on user experience.

That said, the announcement by Microsoft (that they intended to acquire Yahoo!) provided me a 30% return in less than three months. As much as I like some of the long-term potential in the business…30% in two months? Sold at $28.51.

That little zinger comes via my mom while eating dinner this past weekend with me and my brother. Nice to know she sees value in what I do.

To her credit, she has been using email forever, she’s learned to monitor stalk my little sister’s fb, her addiction to QVC has long been replaced by an addiction to eBay and, I believe, she even has a skype account (non eBay related… if, for that matter, any skype accounts are actually eBay related).